5-Hydroxyindole → HCID 67127040, compound

HRID 706871Notes

Reaction equation

HRID 706871 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.F[C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOCCOC.CCOCC>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][C:12]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=3[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 160545-HydroxyindoleHCID 62657Potassium Phosphate, TribasicHCID 2782897Methyl 2,4-Difluorobenzoate

Product 1

HCID 67127040HCID 67127040, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent

Procedure

A mixture of 5-hydroxyindole (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115° C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed twice with water, and brine
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-45614227dc0a4f09b578db9663ce5aeb
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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